@article{roe_kallapur_linderman_viviani_2005, title={Organic synthesis and bioassay of novel inhibitors of JH III epoxide hydrolase activity from fifth stadium cabbage loopers, Trichoplusia ni}, volume={83}, ISSN={["0048-3575"]}, DOI={10.1016/j.pestbp.2005.04.006}, abstractNote={Abstract A series of novel methyl esters with a quaternary ammonium salt, sulfoxide, amine N -oxide, difluorocyclopropane, fluorohydrin, episulfide or epoxide were prepared from undecylenic acid as potential inhibitors of JH III epoxide hydrolase activity from last stadium, wandering cabbage loopers, Trichoplusia ni . Among the non-epoxides examined, the fluorohydrin and sulfoxide (at 100 μM of inhibitor) demonstrated the highest percent inhibition of the insoluble epoxide hydrolase activity while the quaternary ammonium salt, the difluorocyclopropane, and the sulfoxide demonstrated the highest inhibitory activity against the solubilized JH epoxide hydrolase activity. These differences in inhibition between insoluble and solubilized enzyme were in some cases pronounced. For example, the quaternary amine demonstrated no inhibitory activity toward the insoluble enzyme but inhibited 33% of the solubilized JH epoxide hydrolase activity. The incorporation of a cationic character in the amine N -oxide and ammonium salt produced lower inhibitory activity as compared to the sulfoxide, episulfide, difluorocyclopropane, and fluorohydrin for the insoluble epoxide hydrolase, and activity was similar for the solubilized enzyme. Comparing the most potent non-epoxide to the epoxide inhibitors, the fluorohydrin produced 24% inhibition as compared to 85% for the corresponding epoxide and 42% for the epoxide with a shorter backbone chain length for the insoluble epoxide hydrolase activity. For the solubilized epoxide hydrolase activity, difluorocyclopropane demonstrated 34% inhibition as compared to 21% inhibition for the corresponding epoxide. The difluorocyclopropane appeared to be acting as a competitive inhibitor of JH III epoxide hydrolase activity. The I 50 s were greater than 100 μM for all compounds synthesized for both the soluble and solubilized enzymes; the only exceptions were the C11 and C12 epoxides against the insoluble epoxide hydrolase activity (I 50 s = 0.1 and 0.8 μM, respectively). The importance of JH mimicry in epoxide hydrolase inhibition is discussed.}, number={2-3}, journal={PESTICIDE BIOCHEMISTRY AND PHYSIOLOGY}, author={Roe, RM and Kallapur, V and Linderman, RJ and Viviani, F}, year={2005}, pages={140–154} } @article{vanderherchen_isherwood_thompson_linderman_roe_2005, title={Toxicity of novel aromatic and aliphatic organic acid and ester analogs of trypsin modulating oostatic factor to larvae of the northern house mosquito, Culex pipiens complex, and the tobacco hornworm, Manduca sexta}, volume={81}, ISSN={["1095-9939"]}, DOI={10.1016/j.pestbp.2004.09.006}, abstractNote={Eight non-peptidic chemical analogs of trypsin modulating oostatic factor (TMOF, NH2-YDPAP6), an insect hormone inhibiting trypsin biosynthesis in mosquitoes, were synthesized based on the structure of the native peptide. The median lethal concentration (LC50) for the chemical analogs, TMOF and FDPAP (a peptidic analog of TMOF) was estimated for larvae of the northern house mosquito, the Culex pipiens complex, using a static 5-day bioassay. Four of these compounds demonstrated the same larvicidal activity as TMOF, while three of these compounds were 1.2–2.5-fold more active than TMOF. The compounds introduced by injection were toxic to fourth instars of the tobacco hornworm, Manduca sexta, except for TMOF, FDPAP, and PPHEN. Injection of TMOF and FDPAP into fourth stadium and TMOF into second stadium M. sexta had no effect on trypsin activity, growth, or mortality. Apparently the mosquito hormone is inactive in the tobacco hornworm at the developmental stages examined. Three TMOF analogs (CHEA, PHEA, and PHA) demonstrating the highest activity by injection in M. sexta were also found to be toxic by injection in fourth instars of the tobacco budworm, Heliothis virescens, and the cotton bollworm, Helicoverpa zea, as well as adult male German cockroaches, Blattela germanica. A two-choice feeding bioassay with H. virescens indicated that at least one of the TMOF analogs, PHEA, has anti-feeding properties.}, number={2}, journal={PESTICIDE BIOCHEMISTRY AND PHYSIOLOGY}, author={Vanderherchen, MB and Isherwood, M and Thompson, DM and Linderman, RJ and Roe, RM}, year={2005}, month={Feb}, pages={71–84} } @misc{linderman_2004, title={Pesticidal activity of functionalized cyclopropanes}, volume={6,720,450}, number={2004 Apr. 13}, publisher={Washington, DC: U.S. Patent and Trademark Office}, author={Linderman, R. J.}, year={2004} } @misc{linderman_2003, title={Pesticidal activity of functionalized alkenes}, volume={6,521,664}, number={2003 Feb. 18}, publisher={Washington, DC: U.S. Patent and Trademark Office}, author={Linderman, R. J.}, year={2003} } @misc{linderman_roe_thompson_vanderherehen_2003, title={Pesticidal activity of functionalized alkenes}, volume={6,660,770}, number={2003 Dec. 9}, publisher={Washington, DC: U.S. Patent and Trademark Office}, author={Linderman, R. J. and Roe, R. M. and Thompson, D. M. and Vanderherehen, M.}, year={2003} } @misc{borovsky_linderman_2002, title={Pesticidal peptides}, volume={6,413,530}, number={2002 Jul 2}, publisher={Washington, DC: U.S. Patent and Trademark Office}, author={Borovsky, D. and Linderman, R. J.}, year={2002} } @article{coleman_linderman_hodgson_rose_2000, title={Comparative metabolism of chloroacetamide herbicides and selected metabolites in human and rat liver microsomes.}, volume={108}, ISSN={["0091-6765"]}, DOI={10.2307/3434827}, abstractNote={Acetochlor [2-chloro-N-(ethoxymethyl)-N-(2-ethyl-6-methyl-phenyl)-acetamide], alachlor [N-(methoxymethyl)-2-chloro-N-(2,6-diethyl-phenyl)acetamide], butachlor [N-(butoxymethyl)-2chloro-N-(2,6-diethyl-phenyl)acetamide], and metolachlor [2-chloro-N-(2-ethyl-6-methylphenyl)-N-(2-methoxy-1-methylethyl) acetamide] are pre-emergent herbicides used in the production of agricultural crops.These herbicides are carcinogenic in rats: acetochlor and alachlor cause tumors in the nasal turbinates, butachlor causes stomach tumors, and metolachlor causes liver tumors.It has been suggested that the carcinogenicity of these compounds involves a complex metabolic activation pathway leading to a DNA-reactive dialkylbenzoquinone imine.Important intermediates in this pathway are 2-chloro-N-(2,6-diethylphenyl)acetamide (CDEPA) produced from alachlor and butachlor and 2-chloro-N-(2-methyl-6-ethylphenyl)acetamide (CMEPA) produced from acetochlor and metolachlor.Subsequent metabolism of CDEPA and CMEPA produces 2,6-diethylaniline (DEA) and 2-methyl-6-ethylaniline (MEA), which are bioactivated through para-hydroxylationand subsequent oxidation to the proposed carcinogenic product dialkylbenzoquinone imine.The current study extends our earlier studies with alachlor and demonstrates that rat liver microsomes metabolize acetochlor and metolachlor to CMEPA (0.065 nmol/min/mg and 0.0133 nmol/min/mg, respectively), whereas human liver microsomes can metabolize only acetochlor to CMEPA (0.023 nmol/min/mg).Butachlor is metabolized to CDEPA to a much greater extent by rat liver microsomes (0.045 nmol/min/mg) than by human liver microsomes (< 0.001 nmol/min/mg).We have determined that both rat and human livers metabolize both CMEPA to MEA (0.308 nmol/min/mg and 0.541 nmol/min/mg, respectively) and CDEPA to DEA (0.350 nmol/min/mg and 0.841 nmol/min/mg, respectively).We have shown that both rat and human liver microsomes metabolize MEA (0.035 nmol/min/mg and 0.069 nmol/min/mg, respectively) and DEA (0.041 nmol/min/mg and 0.040 nmol/min/mg, respectively).We have also shown that the cytochrome P450 isoforms responsible for human metabolism of acetochlor, butachlor, and metolachlor are CYP3A4 and CYP2B6.}, number={12}, journal={ENVIRONMENTAL HEALTH PERSPECTIVES}, author={Coleman, S and Linderman, R and Hodgson, E and Rose, RL}, year={2000}, month={Dec}, pages={1151–1157} } @article{wu_sa o'neill_brousseau_mcconnell_shultz_linderman_feldheim_2000, title={Synthesis of nanometer-sized hollow polymer capsules from alkanethiol-coated gold particles}, ISSN={["1359-7345"]}, DOI={10.1039/b001019g}, abstractNote={A tripodal alkythiolate ligand has been assembled on gold nanoparticles, which upon metathesis polymerization and particle etching, yields crosslinked spherical hollow polymer capsules.}, number={9}, journal={CHEMICAL COMMUNICATIONS}, author={Wu, ML and SA O'Neill and Brousseau, LC and McConnell, WP and Shultz, DA and Linderman, RJ and Feldheim, DL}, year={2000}, pages={775–776} } @article{harris_thompson_linderman_tomalski_roe_1999, title={Cloning and expression of a novel juvenile hormone-metabolizing epoxide hydrolase during larval-pupal metamorphosis of the cabbage looper, Trichoplusia ni}, volume={8}, ISSN={["1365-2583"]}, DOI={10.1046/j.1365-2583.1999.810085.x}, abstractNote={Abstract}, number={1}, journal={INSECT MOLECULAR BIOLOGY}, author={Harris, SV and Thompson, DM and Linderman, RJ and Tomalski, MD and Roe, RM}, year={1999}, month={Feb}, pages={85–96} } @article{linderman_binet_petrich_1999, title={Enhanced diastereoselectivity in the asymmetric Ugi reaction using a new "convertible" isonitrile}, volume={64}, ISSN={["0022-3263"]}, DOI={10.1021/jo982186e}, abstractNote={ADVERTISEMENT RETURN TO ISSUEPREVCommunicationNEXTADDITION / CORRECTIONThis article has been corrected. View the notice.Enhanced Diastereoselectivity in the Asymmetric Ugi Reaction Using a New “Convertible” IsonitrileRussell J. Linderman, Sophie Binet, and Samantha R. PetrichView Author Information Department of Chemistry, North Carolina State University, Raleigh, North Carolina 27695-8204 Cite this: J. Org. Chem. 1999, 64, 2, 336–337Publication Date (Web):December 31, 1998Publication History Received2 November 1998Published online31 December 1998Published inissue 1 January 1999https://doi.org/10.1021/jo982186eCopyright © 1999 American Chemical SocietyRIGHTS & PERMISSIONSArticle Views1787Altmetric-Citations82LEARN ABOUT THESE METRICSArticle Views are the COUNTER-compliant sum of full text article downloads since November 2008 (both PDF and HTML) across all institutions and individuals. These metrics are regularly updated to reflect usage leading up to the last few days.Citations are the number of other articles citing this article, calculated by Crossref and updated daily. Find more information about Crossref citation counts.The Altmetric Attention Score is a quantitative measure of the attention that a research article has received online. Clicking on the donut icon will load a page at altmetric.com with additional details about the score and the social media presence for the given article. Find more information on the Altmetric Attention Score and how the score is calculated. Share Add toView InAdd Full Text with ReferenceAdd Description ExportRISCitationCitation and abstractCitation and referencesMore Options Share onFacebookTwitterWechatLinked InReddit Read OnlinePDF (37 KB) Get e-AlertsSupporting Info (1)»Supporting Information Supporting Information SUBJECTS:Amides,Peptides and proteins,Reaction products,Stereoselectivity,Ugi reaction Get e-Alerts}, number={2}, journal={JOURNAL OF ORGANIC CHEMISTRY}, author={Linderman, RJ and Binet, S and Petrich, SR}, year={1999}, month={Jan}, pages={336–337} } @article{coleman_liu_linderman_hodgson_rose_1999, title={In vitro metabolism of alachlor by human liver microsomes and human cytochrome P450 isoforms}, volume={122}, ISSN={["0009-2797"]}, DOI={10.1016/S0009-2797(99)00107-6}, abstractNote={Alachlor (2-chloro-N-methoxymethyl-N-(2,6-diethylphenyl)acetamide) is a widely used pre-emergent chloroacetanilide herbicide which has been classified by the USEPA as a probable human carcinogen. The putative carcinogenic metabolite, 2,6-diethylbenzoquinone imine (DEBQI), is formed through a complex series of oxidative and non-oxidative steps which have been characterized in rats, mice, and monkeys but not in humans. A key metabolite leading to the formation of DEBQI is 2-chloro-N-(2,6-diethylphenyl)acetamide (CDEPA). This study demonstrates that male human liver microsomes are able to metabolize alachlor to CDEPA. The rate of CDEPA formation for human liver microsomes (0.0031±0.0007 nmol/min per mg) is significantly less than the rates of CDEPA formation for rat liver microsomes (0.0353±0.0036 nmol/min per mg) or mouse liver microsomes (0.0106±0.0007). Further, we have screened human cytochrome P450 isoforms 1A1, 1A2, 2B6, 2C8, 2C9, 2C18, 2C19, 2D6, 2E1, and 3A4 and determined that human CYP 3A4 is responsible for metabolism of alachlor to CDEPA. Further work is necessary to determine the extent to which humans are able to metabolize CDEPA through subsequent metabolic steps leading to the formation of DEBQI.}, number={1}, journal={CHEMICO-BIOLOGICAL INTERACTIONS}, author={Coleman, S and Liu, SM and Linderman, R and Hodgson, E and Rose, RL}, year={1999}, month={Aug}, pages={27–39} } @article{roe_hodgson_rose_thompson_devorshak_anspaugh_linderman_harris_tomalski_1998, title={Basic principles and rationale for the use of insect genes in bioremediation: esterases, phosphotriesterase, cytochrome P450 and epoxide hydrolase}, volume={2}, number={1998}, journal={Reviews in Toxicology}, author={Roe, R. M. and Hodgson, E. and Rose, R. L. and Thompson, D. M. and Devorshak, C. and Anspaugh, D. D. and Linderman, R. J. and Harris, S. V. and Tomalski, M. D.}, year={1998}, pages={169–178} } @article{el kasmi_wallace_bowden_binet_linderman_1998, title={Controlling interfacial electron-transfer kinetics of cytochrome c with mixed self-assembled monolayers}, volume={120}, ISSN={["0002-7863"]}, DOI={10.1021/ja973417m}, abstractNote={ADVERTISEMENT RETURN TO ISSUEPREVCommunicationNEXTControlling Interfacial Electron-Transfer Kinetics of Cytochrome c with Mixed Self-Assembled MonolayersAsma El Kasmi, Jean Marie Wallace, Edmond F. Bowden, Sophie M. Binet, and Russell J. LindermanView Author Information School of Science and Engineering, Al Akhawayn University Ifrane 53000, Morocco Department of Chemistry, North Carolina State University Raleigh, North Carolina 27695-8204 Cite this: J. Am. Chem. Soc. 1998, 120, 1, 225–226Publication Date (Web):January 14, 1998Publication History Received1 October 1997Revised21 November 1997Published online14 January 1998Published inissue 1 January 1998https://doi.org/10.1021/ja973417mCopyright © 1998 American Chemical SocietyRIGHTS & PERMISSIONSArticle Views1092Altmetric-Citations208LEARN ABOUT THESE METRICSArticle Views are the COUNTER-compliant sum of full text article downloads since November 2008 (both PDF and HTML) across all institutions and individuals. These metrics are regularly updated to reflect usage leading up to the last few days.Citations are the number of other articles citing this article, calculated by Crossref and updated daily. Find more information about Crossref citation counts.The Altmetric Attention Score is a quantitative measure of the attention that a research article has received online. Clicking on the donut icon will load a page at altmetric.com with additional details about the score and the social media presence for the given article. Find more information on the Altmetric Attention Score and how the score is calculated. Share Add toView InAdd Full Text with ReferenceAdd Description ExportRISCitationCitation and abstractCitation and referencesMore Options Share onFacebookTwitterWechatLinked InReddit Read OnlinePDF (44 KB) Get e-AlertsSupporting Info (1)»Supporting Information Supporting Information SUBJECTS:Alcohols,Charge transfer,Fungi,Interfaces,Peptides and proteins Get e-Alerts}, number={1}, journal={JOURNAL OF THE AMERICAN CHEMICAL SOCIETY}, author={El Kasmi, A and Wallace, JM and Bowden, EF and Binet, SM and Linderman, RJ}, year={1998}, month={Jan}, pages={225–226} } @article{roe_anspaugh_venkatesh_linderman_graves_1997, title={A novel geminal diol as a highly specific and stable in vivo inhibitor of insect juvenile hormone esterase}, volume={36}, ISSN={["1520-6327"]}, DOI={10.1002/(SICI)1520-6327(1997)36:3<165::AID-ARCH2>3.0.CO;2-T}, abstractNote={Thio-containing and acetylenic trifluoromethyl ketones were potent inhibitors of insect juvenile hormone (JH) esterase with greater inhibitory activity than aliphatic and α,β-unsaturated homologs. Octylthio-1,1,1-trifluoropropan-2-one was the most potent inhibitor with the greatest equilibrium hydration constant in pure water. However, a keto/hydrate equilibrium was not necessary for JH esterase inhibition. The carbonyl tautomer of 1-octyl [1-(3,3,3-trifluoropropan-2,2- dihydroxy)] sulfone (OTPdOH-sulfone) was not detectable, and yet OTPdOH-sulfone was a potent in vitro inhibitor of JH esterase with an I50 of 1.2 nM. The mechanism of JH esterase inhibition by these compounds is discussed. OTPdOH-sulfone inhibited JH esterase with minimal activity toward insect 1-naphthyl acetate esterase and electric eel acetylcholinesterase. The inhibitor was also active in vivo, selective for JH esterase, and persistent for over 32 h. OTPdOH-sulfone when topically applied to larval and adult cabbage loopers, Trichoplusia ni, elicited juvenoid activity apparently because of the specific in vivo inhibition of JH metabolism. Arch. Insect Biochem. Physiol. 36:165–179, 1997. © 1997 Wiley-Liss, Inc.}, number={3}, journal={ARCHIVES OF INSECT BIOCHEMISTRY AND PHYSIOLOGY}, author={Roe, RM and Anspaugh, DD and Venkatesh, K and Linderman, RJ and Graves, DM}, year={1997}, pages={165–179} } @article{linderman_siedlecki_oneill_sun_1997, title={Conformational bias by a removable substituent. Synthesis of eight-membered cyclic ethers via ring-closing metathesis}, volume={119}, ISSN={["0002-7863"]}, DOI={10.1021/ja9711674}, abstractNote={ADVERTISEMENT RETURN TO ISSUEPREVCommunicationNEXTConformational Bias by a Removable Substituent. Synthesis of Eight-Membered Cyclic Ethers via Ring-Closing MetathesisRussell J. Linderman, James Siedlecki, Stacy A. O'Neil, and Hao SunView Author Information Department of Chemistry North Carolina State University Raleigh, North Carolina 27695-8204 Cite this: J. Am. Chem. Soc. 1997, 119, 29, 6919–6920Publication Date (Web):July 23, 1997Publication History Received14 April 1997Published online23 July 1997Published inissue 1 July 1997https://doi.org/10.1021/ja9711674Copyright © 1997 American Chemical SocietyRequest reuse permissionsArticle Views463Altmetric-Citations61LEARN ABOUT THESE METRICSArticle Views are the COUNTER-compliant sum of full text article downloads since November 2008 (both PDF and HTML) across all institutions and individuals. These metrics are regularly updated to reflect usage leading up to the last few days.Citations are the number of other articles citing this article, calculated by Crossref and updated daily. Find more information about Crossref citation counts.The Altmetric Attention Score is a quantitative measure of the attention that a research article has received online. Clicking on the donut icon will load a page at altmetric.com with additional details about the score and the social media presence for the given article. Find more information on the Altmetric Attention Score and how the score is calculated. Share Add toView InAdd Full Text with ReferenceAdd Description ExportRISCitationCitation and abstractCitation and referencesMore Options Share onFacebookTwitterWechatLinked InReddit Read OnlinePDF (150 KB) Get e-AlertscloseSupporting Info (1)»Supporting Information Supporting Information SUBJECTS:Cyclization,Ethers,Materials,Metathesis,Molecular structure Get e-Alerts}, number={29}, journal={JOURNAL OF THE AMERICAN CHEMICAL SOCIETY}, author={Linderman, RJ and Siedlecki, J and ONeill, SA and Sun, H}, year={1997}, month={Jul}, pages={6919–6920} } @article{linderman_tshering_venkatesh_goodlett_dauterman_roe_1991, title={ORGANOPHOSPHORUS INHIBITORS OF INSECT JUVENILE-HORMONE ESTERASE}, volume={39}, ISSN={["0048-3575"]}, DOI={10.1016/0048-3575(91)90214-7}, abstractNote={Abstract Three classes of organophosphorus inhibitors, O -alkyl ethylphosphonates, enol phosphates, and α-thioalkylphosphonates have been prepared and assayed as inhibitors of insect juvenile hormone (JH) esterase. The O -alkyl ethylphosphonates were prepared from ethylphosphonic dichloride by sequential addition of sodium 4-nitrophenoxide and the appropriate lithium alkoxide. The enol phosphates were prepared via the Perkow reaction from α-chloro aldehydes. Ethyl O -4-nitrophenyl octylthiomethylphosphonate (ENOSP) and ethyl S -phenyl octylthiomethylphosphonothioate (EPOSP) were prepared from diethyl thiomethylphosphonate. The O -alkyl phosphonate series exhibited in vitro activity ( I 50 = 10 −6 to 10 −8 M ) as inhibitors for JH esterase. In in vivo studies, n -hexyl O -4-nitrophenyl ethylphosphonate (ONEP) was a persistent but nonselective inhibitor of JH esterase. The enol phosphates were ineffective JH esterase inhibitors in in vitro and in vivo studies. The α-thioalkylphosphonates ENOSP and EPOSP were very potent JH esterase inhibitors, I 50 = 1.0 × 10 −9 and 4.9 × 10 −9 M , respectively. Both ENOSP and EPOSP were also persistent in vivo inhibitors which exhibited considerable selectivity for JH esterase over α-naphthyl acetate esterase. A kinetic analysis of ENOSP determined that inhibition followed pseudo-first-order kinetics in which a reversible enzyme/inhibitor complex precedes irreversible phosphorylation. The bimolecular rate constant ( k i ) was 6.52 × 10 7 M −1 min −1 , the phosphorylation rate constant ( k 2 ) was 2.66 min −1 , and the dissociation constant ( K d ) was 4.08 × 10 −8 M . The enhanced inhibitory potency of the α-thioalkylphosphonates may be due to anchimeric assistance of the S atom in the phosphorylation step, or to enhanced stability of the EI complex by hydrogen bonding.}, number={1}, journal={PESTICIDE BIOCHEMISTRY AND PHYSIOLOGY}, author={LINDERMAN, RJ and TSHERING, T and VENKATESH, K and GOODLETT, DR and DAUTERMAN, WC and ROE, RM}, year={1991}, month={Jan}, pages={57–73} } @article{linderman_upchurch_lonikar_venkatesh_roe_1989, title={INHIBITION OF INSECT JUVENILE-HORMONE ESTERASE BY ALPHA,BETA-UNSATURATED AND ALPHA-ACETYLENIC TRIFLUOROMETHYL KETONES}, volume={35}, ISSN={["0048-3575"]}, DOI={10.1016/0048-3575(89)90090-4}, abstractNote={A series of β,β-disubstituted-α,β-unsaturated and β-substituted-α-acetylenic fluoroketones have been prepared and assayed as inhibitors of insect juvenile hormone esterase from the cabbage looper, Trichoplusia ni (Hubner) (Lepidoptera: Noctuidae). The most potent inhibitors of each series, 4-methyl-1,1,1-trifluorododec-3-en-2-one 3 and 1,1,1-trifluorododec-3-yn-2-one 15, were also assayed as in vivo inhibitors of juvenile hormone esterase. None of the new compounds assayed were more effective inhibitors than structurally analogous α-thioalkyl substituted trifluoropropanones. The acetylenic series were uniformly more potent inhibitors than the unsaturated series of fluoroketones. The difluoroketone derivatives of the most potent inhibitors were markedly less active. This study clearly reveals that the S atom of α-thioalkyl substituted fluoroketone inhibitors has a more complex function than simply mimicking the site of unsaturation in the natural substrate.}, number={3}, journal={PESTICIDE BIOCHEMISTRY AND PHYSIOLOGY}, author={LINDERMAN, RJ and UPCHURCH, L and LONIKAR, M and VENKATESH, K and ROE, RM}, year={1989}, month={Nov}, pages={291–299} } @article{linderman_leazer_roe_venkatesh_selinsky_london_1988, title={F-NMR-19 SPECTRAL EVIDENCE THAT 3-OCTYLTHIO-1,1,1-TRIFLUOROPROPAN-2-ONE, A POTENT INHIBITOR OF INSECT JUVENILE-HORMONE ESTERASE, FUNCTIONS AS A TRANSITION-STATE ANALOG INHIBITOR OF ACETYLCHOLINESTERASE}, volume={31}, ISSN={["1095-9939"]}, DOI={10.1016/0048-3575(88)90021-1}, abstractNote={Fluoroketones have been developed as highly potent, specific inhibitors of insect juvenile hormone esterase. These compounds are believed to function as transition state analog inhibitors of the enzyme. Of the fluoroketones prepared, 3-octylthio-1,1,1-trifluoropropan-2-one has been extensively studied, yet no analysis of the actual mode of enzyme inhibition has been reported. A 19F-NMR analysis of the inhibition of a hydrolytic enzyme, acetylcholinesterase, by 3-octylthio-1,1,1-trifluoropropan-2-one was carried out. Experiments with phosphorylated acetyl-cholinesterase determined that interaction of the fluoroketone with the enzyme is specific for the esteratic active site serine residue. The carbonyl moiety of the fluoroketone is required for binding and inhibition. The fluoroketone binds to the enzyme active site in a tetrahedral form, indicating that 3-octylthio-1,1,1-trifluoropropan-2-one does function as a transition state analog inhibitor of a hydrolytic enzyme.}, number={2}, journal={PESTICIDE BIOCHEMISTRY AND PHYSIOLOGY}, author={LINDERMAN, RJ and LEAZER, J and ROE, RM and VENKATESH, K and SELINSKY, BS and LONDON, RE}, year={1988}, month={Jun}, pages={187–194} }